Benzoic acid salt of amino benzoic esters



Patented Nov. 6, 1928.

PATENT OFFICE.

' HERMAN SEYDEL, or :naznsmz CITY, NEW JERSEY.

BENZOIG Acrn SALT or AMINO BENZOIG ns'rnns.

No-Drawing'. Application filed April 5,

This invention relates to anew chemical for medicinal use having antiseptic asiwell as anesthetic properties. I

The primary object of the invention is the provision of a new 7 medicinal "compound obtained from benzoic acid and an anesthtic such as para amino benzoyl ethanol which may be appropriately termed a benzoate of an amino benzoic ester.

This invention relates to the provision of a benzoic acid salt of the ethyl ester ofpara amino benzoic acid.

In the formation of t e improved chemical it is preferred to use, by Weight, para amino benzoyl ethanol in the proportion of 57 to 42 %0f benzoic acid. In the manufacture the para amino benzoyl, ethanol is dissolved in the required quantity of dilute hydrochloric acid, and adding the filtered solution to a previously filtered solution of sodium benzoate, from which medium is precipitated a white finely divided powder which can be readily washed and freed from the sodium chloride, which is also formed as a result of the reaction. If the materials used in the reaction are of high purity, it is found unnecessary to refine the product further. For further refining, however, the para amino benzoyl ethanol benzoate may be dissolved in a suitable medium, treated with decolorizing carbon, or refined in any approved way available for organic chemicals of high purity. v

The principal benzoates of amino benzoic esters are those of anesthesin, butesin, pro pesin, procaine, etc., and the characteristicsof these esters are :--ready solubility in oils, and alcohols, and slight solubility in water.

As to the slight solubility in water, the same prompts absorption of the chemical by tissues, and. thereby increases both its antiseptic and anesthetic value.

The ready solubility of the improved chemical in oil permits its being used in ointments, salves, or unguents for the treatment of skin lesions and irritations, such as burns, sunburn, etc.

The ready solubility of the improved medical chemical in alcohol and benzyl alcohol makes possible its use as 'a local anesthetic for the relief of mucous infections, and renders the same of value in the treatment of gumboils, throat infections, and in general wherever the use of benzocaine or benzyl alcohol, or both are indi-' cated.

1927., Serial No. 181,269.

, The solubility of the improved compound is benzyl alcohol also makes possible a dilu- 7 tion of both in such media as pure olive oil, almond 011, or any other oil which may be safely lnjected subcutaneously, and be used ill) for such purposes as the relief of local nerve irritation and particularl the ailment described as pruritus ani, or which the improved compound seems to'afford distinct relief.

One form of the improved chemical may be called para amino benzoyl ethanol benzoate having the chemical formulae:

the structural formulas of which may he represented as follows:

and containing by weight, approximately andja number of other solvents as is obvious.

. 'coocini OCH! NSC] Nm-Hooo can A further proof that the resultant prodnot is a chemical compound is its definite melting point of 7 0 to 71 C. which is much lower than either of its components.

It is intended that the compound will not only cover the benzoic acid salts of the esters of para amino benzoic acid, but also of the ortho and meta amino benzoic acids, and therefore departures may be made from 'the invention within the liberal interpretation of the scope of the claims.

I claim:

1. As new products of manufacture benzoic salts of amino benzoic esters.

2. A new product comprising a benzoate of ethyl amino benzoate.

3. A new product of manufacture comrising the compound C H O CG H NH 4. A new product of manufacture comprising benzoate of an amino benzoic ester in white crystalline powdered form, having 20 a melting point of 70 C. to 71 C.

5. As a new product of manufacture a benzoate of an aromatic acid ester, having an amino group in the aromatic nucleus.

6. As a new product, the substance hav- 25 ing the structural formula NH: HOOC HERMAN SEYDEL. 

